What kind of organisations should a person join at different points in their career?

How can one identify the best kind of organisation to join at different point in one's career?

I think the main thing to do here is to understand what your priorities are and then find something that matches your top 2-3.

I understand that the advice to this question may not be a prescription for all, but how can one identify places that would help them to maximize their learning and growth.

At a more "immediate" level, the main thing to do is to evaluate the engineering manager. We have a 1.5 hour deep dive video about that here.

Zooming out, I personally think one should strive to work at as many different "archetypes" of companies as possible. For example, if you have only ever worked for Big Tech companies, you probably won't learn too much switching into yet another Big Tech company. But if you switch into a small startup, there's going to be way more skills you need to develop in order to add value there.

I kept the above in mind during my career: PayPal (somewhat big, older company) -> Course Hero (50-person startup) -> Meta (massive, Big Tech company) -> Robinhood (medium-sized, pre-IPO)

All 4 companies had very different vibes when I was there, and I really enjoyed being able to experience the entire tech "landscape" through this company diversity.

Personally, I feel that WLB is dependent on a person more than that on the organisation.

I definitely agree to some extent: Many people don't realize that preserving their WLB is something they need to work for - Good WLB is usually not just "handed" to you. However, in many scenarios, you will have an org that has insane deadlines and crazy peer pressure from everyone else over-working and your poor WLB is indeed mostly from the org, not from yourself.

Great question! Or rather, many great questions! I'll break up my response into several separate responses to make it more digestible.

What kind of organisations should a person join at different points in their career?

In a vacuum, I would do something like this:

1. Big Tech company (a place with >1000 engineers) for 2-4 years
2. Whatever you want to do afterwards (which could also be staying at the same company from #1).

For my reasoning behind #1, check out this video. In a nutshell, #1 sets a foundation and healthy "baseline" for your career going forward in terms of skills, level, and compensation.

#2 is where things get interesting, because after you get a great engineering foundation, well, you can do indeed do anything. I think among the best engineers I've seen, it's generally like this after #1:

1. Go to smaller companies to have more impact, usually startups.
2. Revert back to bigger companies as responsibilities outside of work grow (usually getting married and then having kids).

I've also seen people just stay at Big Tech forever or stick to startups and are able to make it work.

In the end, everyone needs to find their own path. I feel the strongest about trying to start at a Big Tech company if you can, but even then, Big Tech isn't for everyone. The main thing that I recommend everyone do is have an honest conversation with themselves every couple months to soul-search and figure out what they want out of their career (and life in general!). I cover that more in this Q&A about switching teams.

Given that a person has joined an organisation, what are the kind of signals that they can identify to see whether the organisation is supportive of their career growth and is indeed the right place to be, for them?

The core thing to look out for is are you getting high-quality, actionable feedback to get better? There are many, many sources where this can come from. Here's some:

1. Your manager - Do your 1:1s feel awkward?
2. Engineering mentors - Are you getting a lot from mentorship?
3. Code review - Are you getting a lot of comments on your pull requests?
4. Feedback on your more public communications (Slack messages, Workplace posts) - It can be a reply to your message or feedback send privately/
5. In meetings (team meetings, tech review) - Tech review is especially rich for this.
6. A healthy performance review system with 360 feedback - This is one of the most powerful mechanisms as it's formal and polished.

Given that there is no list out there to check, how can one make the best suited decisions for their career, not landing at a place they should not be at? What kind of research can a person do before joining an organisation?

The internet indeed has no good list to check. I feel like Glassdoor leans a bit too positive and Blind is way too negative. I think the main things to do are:

1. Go through your network - This is by far the most effective thing to do as these should be people you trust. For advice on how to build a large, high-quality network, I recommend checking out this Q&A and this one.

2. Talk to the engineering manager and team - "Reverse interview" them during the interview and see if you can talk to them prior to accepting the offer. How much signal you get from this depends on your ability to effectively communicate, which I made an entire series about.

How do you identify the honest signal from the noise all around?

I think the important thing is to understand people's incentives. As you mentioned, managers will paint that "rosy picture" as it's very baked into their growth incentives to hire as many people as possible. This is why a simple way to get better signal on a team is to talk to the engineers on it as well, not just the manager. The engineers are less tied to the destiny of the team (they may even be considering a move), so they have less incentive to be "overly optimistic" with their evaluation of the team.

Aside from that, to be honest, there's no magic, super accessible way to get this great signal. I think it comes down to 2 things:

1. How well you are able to "read" people (intonation, body language, etc) to judge their honesty
2. Building up a deep network of people you trust (who also trust you) who are willing to be 100% real with you

For #2, I highly recommend checking out my series on effective communication.

If you find an organisation not good for you after you join there, how quick is it too quick to leave? How much time should you spend there before you can make a judgement about the same?

I generally try to stay in an org for at least a year. If you're thinking of not only leaving the org but leaving the entire company (instead of switching teams), I recommend trying to stay at least 2 years at the company. All that being said:

1. If you feel like a job is toxic, leave ASAP - No job is worth your mental health and overall sanity. Mental health is closely linked to physical health as well.
2. You should always be making judgments - Things in tech change fast, so it's important to reflect regularly. I think taking some time every week to reflect on how things are going is a good cadence. However, don't over-index on just 1 week (e.g. "This 1 week was bad, therefore I will leave the company."). Gather these data points week after week and see how things are trending overall. If after a few months, the trend is poor, then yes, you can think about moves.
3. Meet the situation halfway - It is impossible to find the perfect team for you. A common failure mode I see among engineers is that they don't feel empowered to improve their current situation and switch teams constantly. The ability to turn a bad/mediocre situation into a good one is a crucial skill for senior/staff engineers in particular, so constantly "running away" is unhealthy. In terms of how to do that, every situation is different, so I recommend asking questions into Taro for this. The important thing is that you feel empowered to fix things as opposed to expecting the perfect team to fall into your lap.

For more thoughts on this, I recommend checking out this Q&A around when it's time to switch teams/companies.